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Hydroxycinnamic acid amides (HCAAs), diversely distributed secondary metabolites in plants, play essential roles in plant growth and developmental processes. Most current approaches can be used to analyze a few known HCAAs in a given plant. A novel method for comprehensive detection of plant HCAAs is urgently needed. In this study, a deep annotation method of HCAAs was proposed on the basis of ultra-high-performance liquid chromatography-high-resolution mass spectrometry (UHPLC-HRMS) and its in silico database of HCAAs. To construct an in silico UHPLC-HRMS HCAAs database, a total of 846 HCAAs were generated from the most common phenolic acid and polyamine/aromatic monoamine substrates according to possible biosynthesis reactions, which represent the structures of plant-specialized HCAAs. The characteristic MS/MS fragmentation patterns of HCAAs were extracted from reference mixtures. Four quantitative structure-retention relationship (QSRR) models were developed to predict retention times of mono-trans-HCAAs (aromatic amines conjugates), mono-trans-HCAAs (aliphatic amines conjugates), bis-HCAAs, and tris-HCAAs. The developed method was applied for identifying HCAAs in seeds (maize, wheat, and rice), roots (rice), and leaves (rice and tobacco). A total of 79 HCAAs were detected: 42 of them were identified in these plants for the first time, and 20 of them have never been reported to exist in plants. The results showed that the developed method can be used to identify HCAAs in a plant without prior knowledge of HCAA distributions. To the best of our knowledge, it is the first UHPLC-HRMS database developed for effective deep annotation of HCAAs from nontargeted UHPLC-HRMS data. It is useful for the identification of novel HCAAs in plants.

analytical chemistry

Deep Annotation of Hydroxycinnamic Acid Amides in Plants Based on Ultra-High-Performance Liquid Chromatography–High-Resolution Mass Spectrometry and Its In Silico Database